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Southold, NY 55+ active adult communities & homes for sale
94 communities near Southold
149 homes near Southold
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3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
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1,500 homes
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
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512 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
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4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
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588 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
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55+ age-restricted
|
Built 1985 - 1999
|
343 homes
5 rating (2 reviews)
![Fairfield at St. James]()
$300ks
- $500ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
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Built 1972 - 1989
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653 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
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Built 2004 - present
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835 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
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55+ age-restricted
|
Built 2013 - present
|
150 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
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$500ks
- $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
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76 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
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55+ age-restricted
|
Built 2005 - 2013
|
189 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
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55+ age-restricted
|
Built 2019 - present
|
125 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
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70 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$500ks
- $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
$600ks
- $700ks
Granite Woods, Middlebury, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
24 homes
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
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$700ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
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55+ age-restricted
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Built 2005 - 2011
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82 homes
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only
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55+ age-restricted
|
Built 2003 - 2006
|
69 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$200ks
- $300ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
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Built 2013 - present
|
31 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$400ks
- $700ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
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246 homes
$300ks
- $400ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
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16 homes
$200ks
- $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
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Questions? Call us:
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$300ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
$300ks
- $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
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67 homes
$400ks
- $500ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (1 reviews)
![Sunrise Village]()
$400ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
$300ks
Strathmore Gate East, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1970 - 1975
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174 homes
$500ks
- $600ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
$800ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
|
Built 2013 - 2017
|
43 homes
Want to learn more about 55+ communities in Southold?
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Questions? Call us:
(631) 407-2675
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
New
Newington Ridge Preserve
![2 DEMING FARM DR 2, NEWINGTON, CT, 06111, Newington, CT 06111]()
2 beds
|2 baths
|1,812 sq ft
2 DEMING FARM DR 2, NEWINGTON, CT, 06111
Community: Newington Ridge Preserve
MLS 24156287 • mygoodagent, Joseph Cafasso
New
The Manors at The Colony Preserve
![41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967]()
2 beds
|2 baths
|1,557 sq ft
|Condo
41 GREENTREE CT, BROOKHAVEN, NY, 11967
Community: The Manors at The Colony Preserve
MLS 964099 • Gateway to The Hamptons R E, Dari A....
New
Fairfield at St. James
![201 BENTLEY CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
MLS 963252 • Douglas Elliman Real Estate, Lina Lo...
New
Heritage Village
![191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24156103 • Century 21 Bette Real Estate, Just...
New
Autumn Fields
![11 PARTRIDGE RUN 11, ENFIELD, CT, 06082, Enfield, CT 06082]()
2 beds
|2 baths
|1,296 sq ft
|Condo
11 PARTRIDGE RUN 11, ENFIELD, CT, 06082
Community: Autumn Fields
MLS 24155377 • Berkshire Hathaway NE Prop., Laura...
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New
Leisure Knoll
![2 BEDFORD CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 964735 • Signature Premier Properties, Lisa M...
New
Oronoque Village
![483 COMMANCHE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
483 COMMANCHE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24154522 • Coldwell Banker Realty, Christine ...
The Manors at The Colony Preserve
![21 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967]()
2 beds
|2 baths
|1,557 sq ft
|Condo
21 GREENTREE CT, SHIRLEY, NY, 11967
Community: The Manors at The Colony Preserve
MLS 963693 • Coldwell Banker M&D Good Life, There...
Encore Atlantic Shores
![135 CHOPIN PL, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|2 baths
|2,233 sq ft
|Condo
135 CHOPIN PL, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 961941 • Corcoran, Merle Buff
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Heritage Village
![411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24155104 • Berkshire Hathaway NE Prop., Bonni...
Sunrise Village
![71 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
MLS 963805 • Signature Premier Properties, Debora...
Spring Lake Village
![41 COACH DR # 41, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,232 sq ft
|Condo
41 COACH DR # 41, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24154460 • Calcagni Real Estate, Donna Pelleg...
The Village at Hunt Glen
![59 HUNT GLEN DR 59, GRANBY, CT, 06035, Granby, CT 06035]()
2 beds
|4 baths
|1,848 sq ft
59 HUNT GLEN DR 59, GRANBY, CT, 06035
Community: The Village at Hunt Glen
MLS 24155492 • Berkshire Hathaway NE Prop., Nancy...
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Heritage Village
![865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24155103 • Showcase Realty, Inc., Gregory Bal...
Regency at Prospect
![50 LILAC LN 50, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|2 baths
|1,503 sq ft
|Condo
50 LILAC LN 50, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24154825 • Showcase Realty, Inc., Scott Marti...
Leisure Knoll
![498 CRANSTON LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 963436 • Coldwell Banker American Homes, Mary...
Fairfield at St. James
![1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|750 sq ft
|House
1205 GOTHAM DR, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 963050 • Realty Connect USA LLC, Annmarie Rig...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Heritage Village
![1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24154431 • Carey & Guarrera Real Estate, Alet...
Encore at Lake Grove
![51 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755]()
2 beds
|3 baths
|1,409 sq ft
|Condo
51 SYMPHONY DR, LAKE GROVE, NY, 11755
Community: Encore at Lake Grove
MLS 962663 • Signature Premier Properties, Karen ...
Leisure Village
![306 TORQUAY CT E, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
306 TORQUAY CT E, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 960743 • Leisure Living Realty Inc, Paulina R...
Heritage Village
![972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24154574 • Berkshire Hathaway NE Prop., Bonni...
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Spring Lake Village
![6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
3 beds
|3 baths
|1,471 sq ft
|Condo
6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24154583 • eXp Realty, Eric Christmas
Woodridge Strathmore Terrace
![35 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,240 sq ft
|Condo
35 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 959098 • Exit Realty Achieve, Laura Kraker E-...
Glenwood Village
![181 GLYNWOOD 181, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|1 baths
|1,100 sq ft
|Manufactured On Land
181 GLYNWOOD 181, RIVERHEAD, NY, 11901
Community: Glenwood Village
MLS 958982 • Coldwell Banker M&D Good Life, Lynn ...
Encore Atlantic Shores
![179 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|3 baths
|2,900 sq ft
|Condo
179 MELODY CT, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 959599 • Douglas Elliman Real Estate, Enzo Mo...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|2,199 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24154316 • Serhant Connecticut, LLC, Carmen D...
Heritage Village
![170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152831 • Ascend Realty LLC, Michael Monteir...
Leisure Knoll
![206 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 960634 • Leisure Living Realty Inc, Paulina R...
Glenwood Village
![1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,050 sq ft
|Mobile Home
1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 960267 • Old Orchard Estates R E Inc, Matthew...
Leisure Glen
![530 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 957040 • Signature Premier Properties, Mildre...
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Spring Lake Village
![40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489]()
2 beds
|2 baths
|1,211 sq ft
|Condo
40 HICKORY HL # 40, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
MLS 24153678 • Realty 3 CT, Shelly Meister Zamudi...
Heritage Village
![575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152837 • Drakeley Real Estate, Inc., Shelle...
Heritage Village
![701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24153612 • Century 21 Limitless, Kyle Seyboth
Leisure Village
![258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
258 NEWCASTLE CT F, RIDGE, NY, 11961
Community: Leisure Village
MLS 958463 • Leisure Living Realty Inc, Paulina R...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Oak Meadow Estates
![65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791]()
2 beds
|4 baths
|2,164 sq ft
|Condo
65 OAK MEADOW LN # 65, HARWINTON, CT, 06...
Community: Oak Meadow Estates
MLS 24153507 • Northwest CT Realty, Leslie Tapia-...
South Pond Village
![81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002]()
2 beds
|2 baths
|1,204 sq ft
|Condo
81 SILO WAY 81, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24151413 • Berkshire Hathaway NE Prop., Sandy...
Leisure Knoll
![304 KINGSTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,000 sq ft
|Condo
304 KINGSTON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 959588 • Howard Hanna Coach, Kalliopi C. Suar...
Oronoque Village
![133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|2,038 sq ft
|Condo
133 BANNOCK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24153059 • William Raveis Real Estate, Joseph...
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Heritage Village
![914 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,144 sq ft
|Condo
914 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152900 • Coldwell Banker Realty, Douglas Co...
Chatfield Farms
![8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,610 sq ft
|Condo
8 WOODLAND PATH 8, BEACON FALLS, CT, 064...
Community: Chatfield Farms
MLS 24153080 • KW Legacy Partners, Mela Veltri Ca...
Frequently Asked Questions
In Southold, there is 1 small community with less than 500 homes.
The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.
No, there are no gated 55+ communities in Southold.
On average, listings in 55+ community in Southold stay on the market for around 169 days. The average price of homes for sale in this community is approximately $527,500, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $527,500.
Want more information about active adult communities around Southold?
Want to learn more about 55+ communities in Southold?
149
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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Feb 27, 2026.
This application does not include information on all of the properties available for sale at this time.
